US20250197340A1 - Method for preparation of high-purity (meth)acrylic acid - Google Patents

Method for preparation of high-purity (meth)acrylic acid Download PDF

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US20250197340A1
US20250197340A1 US18/707,678 US202318707678A US2025197340A1 US 20250197340 A1 US20250197340 A1 US 20250197340A1 US 202318707678 A US202318707678 A US 202318707678A US 2025197340 A1 US2025197340 A1 US 2025197340A1
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meth
acrylic acid
absorption
absorption column
column
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Sung Jin Yoo
Kyung Soo Jang
Sung Kyu Lee
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LG Chem Ltd
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LG Chem Ltd
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Assigned to LG CHEM, LTD. reassignment LG CHEM, LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: JANG, KYUNG SOO, LEE, SUNG KYU, YOO, SUNG JIN
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
    • C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation

Definitions

  • the present invention relates to a method for preparation of high-purity (meth)acrylic acid.
  • (Meth)acrylic acid is generally prepared by a method of subjecting a compound such as propane, propylene, and (meth)acrolein to a gas phase oxidation reaction in the presence of a catalyst.
  • propane, propylene, and the like are converted through (meth)acrolein into (meth)acrylic acid by a gas phase oxidation reaction in the presence of an appropriate catalyst in a reactor, and a mixed gas including (meth)acrylic acid, unreacted propane or propylene, (meth)acrolein, inert gas, carbon dioxide, water vapor, and various organic by-product by the reaction (such as acetic acid, low-boiling point by-products, and high-boiling point by-products) is obtained in a latter stage of the reactor.
  • a mixed gas including (meth)acrylic acid, unreacted propane or propylene, (meth)acrolein, inert gas, carbon dioxide, water vapor, and various organic by-product by
  • the (meth)acrylic acid-containing mixed gas is brought into contact with an absorption solvent such as water in an absorption column to be recovered as a (meth)acrylic acid solution. Further, as a subsequent process for recovering the (meth)acrylic acid included in the (meth)acrylic acid solution, it is common to involve processes such as extraction, distillation, and purification. In order to improve recovery efficiency of the (meth)acrylic acid, various methods of adjusting process conditions, process order, or the like have been suggested.
  • the absorption solvent such as water used in the absorption column has a high specific heat
  • significantly high energy usage is demanded in separating by-products from the (meth)acrylic acid solution including the absorption solvent through a process such as distillation.
  • the subsequent process is simplified and shortened for reducing the energy usage, the energy usage can be decreased, but it is difficult to obtain high-purity (meth)acrylic acid.
  • an object of the present invention is to provide a method for recovering (meth)acrylic acid, which can further reduce energy usage in a purification process and simplify a subsequent process.
  • a method for preparation of (meth)acrylic acid includes: bringing a mixed gas including (meth)acrylic acid into contact with an absorption solvent in an absorption column; supplying a first (meth)acrylic acid solution discharged from a lower portion of the absorption column to a high-boiling point by-product separation column and supplying an upper discharge stream of the high-boiling point by-product separation column to a crystallizer; supplying a second (meth)acrylic acid solution discharged from a side portion of the absorption column to the crystallizer; and obtaining (meth)acrylic acid crystallized in the crystallizer and circulating a mother liquor recovered in the crystallizer to the absorption column.
  • FIG. 2 is a process flow chart showing a method for preparation of (meth)acrylic acid according to the comparative example.
  • a method for preparation of (meth)acrylic acid including: bringing a mixed gas including (meth)acrylic acid into contact with an absorption solvent in an absorption column; supplying a first (meth)acrylic acid solution discharged from a lower portion of the absorption column to a high-boiling point by-product separation column and supplying an upper discharge stream of the high-boiling point by-product separation column to a crystallizer; supplying a second (meth)acrylic acid solution discharged from a side portion of the absorption column to the crystallizer; and obtaining (meth)acrylic acid crystallized in the crystallizer and circulating a mother liquor recovered in the crystallizer to the absorption column, is provided.
  • the method for preparation of (meth)acrylic acid can include bringing a mixed gas including (meth)acrylic acid into contact with an absorption solvent in an absorption column 100 .
  • the mixed gas including (meth)acrylic acid is a concept which collectively refers to gas phase components discharged from a reactor 10 which produces (meth)acrylic acid by a gas phase oxidation reaction.
  • the mixed gas including (meth)acrylic acid can be prepared as follows.
  • a reaction gas including gas containing oxygen and a raw material compound is supplied to a reactor 10 provided with a catalyst through a reaction gas supply line 1 , and is subjected to a gas phase oxidation reaction in the presence of a catalyst in the reactor 10 to obtain the mixed gas including (meth)acrylic acid.
  • the gas containing oxygen can be air.
  • the raw material compound can be one or more compounds selected from the group consisting of propane, propylene, butane, 1-butylene, t-butylene, and (meth)acrolein, and specifically, the raw material compound can include propylene.
  • the reaction gas supplied to the reactor 10 can further include a recirculation gas which is recovered from an upper portion of the absorption column 100 and recirculated. Therefore, the mixed gas including (meth)acrylic acid can be a reaction product by the gas phase oxidation reaction of a reactant including air, the raw material compound, and the recirculation gas, in the reactor 10 .
  • the recirculation gas can be derived from the upper portion of the absorption column 100 described later. That is, the mixed gas comes into contact with the absorption solvent in the absorption column 100 , and a non-condensable gas which is not dissolved in the absorption solvent can be discharged as an upper discharge stream 110 of the absorption column 100 .
  • the non-condensable gas can include impurities such as acetic acid, inert gas, an unreacted raw material compound, a small amount of (meth)acrylic acid which is not dissolved in the absorption solvent, and the like.
  • a part 3 of the upper discharge stream 110 of the absorption column can be supplied to a cooling tower 20 , and the rest 120 can be supplied to a waste gas incinerator and discarded.
  • An amount of the (meth)acrylic acid in the upper discharge stream 110 of the absorption column can be 0.03 mol % to 0.5 mol %.
  • the cooling tower 20 is provided with an absorption solvent supply line 5 in the upper portion, and the absorption solvent can be supplied from the absorption solvent supply line 5 into the cooling tower 20 .
  • the absorption solvent can come into contact with the non-condensable gas included in the part 3 of the upper discharge stream 110 of the absorption column.
  • Components included in the non-condensable gas for example, acetic acid and (meth)acrylic acid which is not dissolved in the absorption solvent in the absorption column 100 are dissolved in the absorption solvent, and can be discharged as a lower discharge stream of the cooling tower 20 .
  • the lower discharge stream of the cooling tower 20 can be resupplied to the absorption column 100 , and the lower discharge stream of the cooling tower 20 can form a mixed stream with a separately supplied absorption solvent stream 6 and be supplied to the absorption column 100 .
  • the supply of the absorption solvent to the absorption column 100 can be performed by one or more supply methods of a supply through an absorption solvent supply line 5 provided in the upper portion of the cooling tower 20 and a direct supply 6 to the absorption column 100 , and the direct supply 6 to the absorption column 100 can be a supply to the absorption column 100 after forming a mixed stream with the lower discharge stream of the cooling tower 20 .
  • a supply amount of the absorption solvent supplied to the absorption column 100 can be determined within a range where an amount of the (meth)acrylic acid in the lower portion of the absorption column 100 can be maintained at 85 wt % or more.
  • the absorption solvent supplied to the cooling tower 20 and the absorption solvent supplied to the absorption column 100 can be the same.
  • the absorption solvent can include water such as tap water and deionized water, and can include circulation process water introduced from other processes (e.g., water phase recirculated from an extraction process and/or a distillation process).
  • the absorption solvent can include a small amount of organic by-products (e.g., acetic acid) introduced from other processes.
  • a recirculation gas transfer line 4 provided in the upper portion of the cooling tower 20 as a recirculation gas.
  • the recirculation gas can be supplied to the reactor 10 so that it can be used in the gas phase oxidation reaction for preparation of (meth)acrylic acid which proceeds in the reactor 10 .
  • the recirculation gas can be mixed with the reaction gas and supplied to the reactor 10 , and can be supplied to the reactor 10 through a separate line from the line 1 to which the reaction gas is supplied.
  • acetic acid and (meth)acrylic acid in the non-condensable gas supplied from the absorption column 100 are dissolved in the absorption solvent in the cooling tower 20 and can be recirculated to the absorption column 100 .
  • the acetic acid in the system can be induced to be discharged as much as possible to the upper discharge stream 110 of the absorption column to obtain high-purity (meth)acrylic acid and minimize loss of (meth)acrylic acid.
  • the amount of the absorption solvent in the recirculation gas which is circulated from the cooling tower 20 to the reactor 10 can be reduced by lowering a temperature inside the cooling tower 20 . That is, by reducing the amount of moisture (water) in the recirculation gas when the absorption solvent is water, an amount of moisture in a stream supplied from the reactor 10 to the absorption column 100 can be lowered, and thus, even the amount of moisture in the absorption column 100 can be lowered.
  • the amount of moisture in the recirculation gas can be 1 wt % to 10 wt %, specifically 3 wt % to 5 wt %.
  • An upper temperature of the cooling tower 20 for this can be 35° C. to 55° C., specifically 35° C. to 45° C.
  • an excessive refrigerant is consumed as compared with a reduction effect of the amount of moisture included in the recirculation gas or a refrigerant at a lower temperature is needed, and thus, there may be no great benefit in terms of efficient energy use.
  • the upper temperature of the cooling tower 20 is higher than 55° C., an amount of the absorption solvent (moisture) included in the recirculation gas transfer line 4 is excessively increased, and thus, it can be difficult to obtain a high-concentration (meth)acrylic acid solution discharged from the absorption column 100 .
  • the temperature control of the upper portion of the cooling tower 20 is performed by a heat exchanger provided in the lower portion of the cooling tower 20 , and specifically, can be performed by circulating a part of the lower stream of the cooling tower 20 to the heat exchanger and the cooling tower 20 . Meanwhile, the upper portion of the cooling tower 20 can be operated under normal pressure operation conditions.
  • a process for obtaining the (meth)acrylic acid solution by supplying the mixed gas 2 including (meth)acrylic acid to the absorption column 100 through a reactor discharge line and bringing the gas into contact with the absorption solvent in the absorption column 100 can be performed.
  • the mixed gas including (meth)acrylic acid produced by a synthesis reaction of (meth)acrylic acid, organic by-products, and absorption solvent steam can be brought into contact with the absorption solvent in the absorption column 100 to obtain the (meth)acrylic acid solution, specifically, first and second (meth)acrylic acid solutions.
  • the kind of absorption column 100 can be determined considering contact efficiency of the mixed gas and the absorption solvent and the like, and for example, can be a packed column type absorption column or a multistage tray type absorption column.
  • a filler such as a Raschig ring, a Pall ring, a saddle, a gauze, and a structured packing can be applied.
  • the mixed gas 2 can be supplied to the lower portion of the absorption column 100 , and the absorption solvent, specifically the absorption solvent including water can be supplied to the upper portion of the absorption column 100 .
  • the absorption column 100 can be operated at an internal pressure of 1 to 1.5 bar or 1 to 1.3 bar and at an internal temperature of 50 to 120° C. or 50 to 100° C., considering the condensation conditions of (meth)acrylic acid, a moisture content depending on a saturated water vapor pressure, and the like.
  • the first (meth)acrylic acid solution discharged from the lower portion of the absorption column 100 is obtained, and the second (meth)acrylic acid solution discharged from the side portion of the absorption column 100 can be obtained.
  • the amount of the (meth)acrylic acid in the first and second (meth)acrylic acid solutions discharged from the absorption column 100 can be 85 wt % to 99 wt %, specifically 85 wt % to 95 wt %. This is a higher level than the amount of the meth) acrylic acid in the (meth)acrylic acid solution discharged from the conventional absorption column.
  • the second (meth)acrylic acid solution can be directly supplied to the crystallizer 300 without undergoing a separate purification process or separation process for the second (meth)acrylic acid solution, and thus, overall process energy can be reduced, and also, high-purity (meth)acrylic acid can be obtained in the crystallizer 300 .
  • the second (meth)acrylic acid solution having a high (meth)acrylic acid concentration can be implemented by minimizing the absorption solvent component in the recirculation gas which is recirculated from the cooling tower 20 to the reactor 10 , minimizing the input amount and used amount of the absorption solvent supplied to the cooling tower 20 and the absorption column 100 , and furthermore, for example, setting the number of discharge stages of the second (meth)acrylic acid solution discharged from the absorption column 100 .
  • the first (meth)acrylic acid solution can be discharged from the lowest stage of the absorption column 100
  • the second (meth)acrylic acid solution can be discharged from the side portion at a height of 80% to 99%, specifically 80% to 90% from top to bottom of the absorption column 100 .
  • the absorption solvent (moisture) and the amount of the high-boiling point by-product in the discharged second (meth)acrylic acid solution can be minimized.
  • the second (meth)acrylic acid solution of including high-concentration (meth)acrylic acid can be directly supplied to the crystallizer 300 .
  • the amount of the absorption solvent discharged through the side portion of the absorption column is increased, and thus, absorption performed at the position lower than the side portion of the absorption column may not be sufficient so that the amount of (meth)acrylic acid lost from the upper portion of the absorption column may be increased.
  • the second (meth)acrylic acid solution is discharged from a lower position than the position of 99% from top to bottom of the absorption column 100 , the amount of the high-boiling point by-product is increased, and thus, it becomes also inappropriate to supply the second (meth)acrylic acid solution to the crystallizer 300 .
  • the amount of the (meth)acrylic acid in the second (meth)acrylic acid solution can be higher than the amount of the (meth)acrylic acid in the first (meth)acrylic acid solution. Since relatively heavy high-boiling point by-products are concentrated at the lowest stage portion of the absorption column 100 , the amount of the (meth)acrylic acid in the second (meth)acrylic acid solution related to the side portion of the absorption column 100 in which almost no high-boiling point by-products are present can be higher than the amount of the (meth)acrylic acid in the first (meth)acrylic acid solution.
  • the mixed gas can be brought into contact with the absorption solvent in the absorption column 100 , a non-condensable gas which is not dissolved in the absorption solvent can be discharged to the upper discharge stream 110 of the absorption column 100 , a part 3 of the upper discharge stream 110 of the absorption column can be supplied to the cooling tower 20 , and the rest 120 can be supplied to a waste gas incinerator and discarded, as described above.
  • the first (meth)acrylic acid solution can be supplied to a high-boiling point by-product separation column 200 along a first (meth)acrylic acid solution stream 150
  • the second (meth)acrylic acid solution can be supplied to the crystallizer 300 along a second (meth)acrylic acid solution stream 160 .
  • the first (meth)acrylic acid solution supplied to the high-boiling point by-product separation column 200 is distilled to be separated into a lower fraction including the high-boiling point by-products and an upper fraction including a high content of (meth)acrylic acid by removing the high-boiling point by-products.
  • the upper fraction of the high-boiling point by-product separation column 200 can be discharged as an upper discharge stream of the high-boiling point by-product separation column and supplied to the crystallizer 300 , and the lower fraction of the high-boiling point by-product separation column 200 can be discharged as a lower discharge stream 220 of the high-boiling point by-product separation column and discarded or recycled through a separate purification process.
  • the amount of the (meth)acrylic acid in the upper discharge stream of the high-boiling point by-product separation column 200 can be 85 wt % to 99 wt %, 90 wt % to 99 wt %, or specifically 90 wt % to 95 wt %.
  • the side discharge stream 160 of the absorption column 100 including the second (meth)acrylic acid solution and the upper discharge stream 210 of the high-boiling point by-product separation column 200 can be supplied to the crystallizer 300 .
  • the (meth)acrylic acid included in the (meth)acrylic acid solution supplied to the crystallizer 300 can be recrystallized through a crystallization process and obtained as recrystallized high-purity (meth)acrylic acid.
  • the crystallization process can be performed under common conditions.
  • the crystallization method for obtaining a product by crystallization in the present invention can be suspension crystallization and layer crystallization without limitation, can be continuous or batchwise, and can be performed in one stage or two stages or more.
  • the (meth)acrylic acid is dynamically crystallized to be provided as high-purity (meth)acrylic acid.
  • the (meth)acrylic acid solution can be first allowed to flow on a tube inner wall in a falling film form. Further, the temperature of the tube can be adjusted to a freezing point of (meth)acrylic acid or lower to form a crystal in the tube inner wall. Then, the temperature of the tube can be raised to near the freezing point of (meth)acrylic acid to sweat about 5 wt % of (meth)acrylic acid. Further, the mother liquor sweated from the tube is removed and the crystal formed in the tube inner wall is recovered, thereby obtaining the high-purity crystallized (meth)acrylic acid.
  • the mother liquor can refer to a solution which is the (meth)acrylic acid solution introduced to the crystallizer 300 from which the crystallized (meth)acrylic acid has been removed.
  • the mother liquor can include acetic acid, an absorption solvent, and a low-boiling point material.
  • Separation of the mother liquor and the crystallized (meth)acrylic acid can be performed using a solid-liquid separation device, for a example, belt filter, a centrifuge, and the like.
  • the mother liquor can be discharged from the crystallizer and circulated to the absorption column 100 along a mother liquor circulation line 310 .
  • the mother liquor can be directly supplied to the absorption column 100 without undergoing a separate purification process or separation process. That is, a ratio of a flow rate when the mother liquor is introduced to the absorption column to a flow rate when the mother liquor recovered in the crystallizer 300 is discharged from the crystallizer can be 0.99 to 1.01, more specifically 1. Meanwhile, by not performing a separate process for the mother liquor, for example, a distillation process, the process is simplified, and the absorption solvent included in the mother liquor, specifically water, does not need to be distilled, and thus, energy costs can be greatly decreased.
  • a mixed gas 2 having a composition of (meth)acrylic acid (7.0 mol %), water (11.8 mol %), a high-boiling point material (0.09 mol %), and inert gas (80.6 mol %) was obtained by a gas phase oxidation reaction of a reactant including air (oxygen), a raw material compound (propylene), and a recirculation gas 4 in the presence of a catalyst in a reactor 10 .
  • the mixed gas 2 was added to a 22nd stage from the top of an absorption column 100 at a temperature of 164° C.
  • a pressure in the upper portion of the absorption column 100 was 1.1 bar
  • a temperature in the lower portion of the absorption column 100 was 96.4° C.
  • an absorption solvent (water) added to the absorption column 100 was supplied through a stream 6 directly supplied to the absorption column and a lower discharge stream of the cooling tower 20 .
  • the absorption solvent was added to the upper portion of the absorption column 100 at a flow rate of 6.6 wt % with respect to the flow rate of the mixed gas 2 .
  • the mother liquor 310 circulated from the crystallizer described later was added to the 15th stage position from the top of the absorption column 100 at a mass flow rate of 1.3 times the flow rate of the absorption solvent introduced to the absorption column 100 .
  • a ratio of the mass flow rate when the mother liquor recovered from the crystallizer 300 was introduced to the absorption column 100 to the flow rate when the recovered mother liquor was discharged from the crystallizer 300 was 1.
  • An upper discharge stream 110 of the absorption column including a non-condensable gas, a first (meth)acrylic acid solution stream 150 including the first (meth)acrylic acid solution, and a second (meth)acrylic acid solution stream 160 including the second (meth)acrylic acid solution were obtained by an absorption process performed in the absorption column 100 .
  • An amount of the (meth)acrylic acid included in the upper discharge stream 110 of the absorption column was 0.146 mol %.
  • a part 3 of the upper discharge stream of the absorption column was supplied to a cooling tower 20 , and the rest 120 was discarded out of the system.
  • the non-condensable gas included in the part 3 of the upper discharge stream of the absorption column and the absorption solvent supplied from the absorption solvent supply line 5 were brought into contact in the cooling tower 20 , and a lower discharge stream of the cooling tower 20 including the absorption solvent and components dissolved in the absorption solvent (acetic acid and (meth)acrylic acid which was not dissolved in the absorption solvent in the absorption column) were obtained and gas (recirculation gas) which was not dissolved in the absorption solvent was supplied to the reactor 10 through a recirculation gas transfer line 4 .
  • a part of the lower discharge stream of the cooling tower 20 was supplied to the absorption column 100 , and the rest was circulated to the cooling tower 20 . At this time, an amount of moisture in the recirculation gas 4 was 4.4 wt %.
  • the first (meth)acrylic acid solution 150 discharged from the bottom of the absorption column 100 included (meth)acrylic acid (85.9 wt %), acetic acid (1.3 wt %), water (4.2 wt %), furfural (3.2 wt %), and maleic acid (5.0 wt %)
  • the second (meth)acrylic acid solution stream 160 was obtained at a flow rate of 7.3 times the mass flow rate of the first (meth)acrylic acid solution stream 150 .
  • the mass flow rate of the absorption solvent included in the first and second (meth)acrylic acid solutions was increased by 30 wt % with respect to the flow rate of the absorption solvent introduced to the absorption column 100 .
  • the mixed stream of the upper discharge stream 210 of the high-boiling point by-product separation column and the second (meth)acrylic acid solution stream 160 was crystallized in the crystallizer 300 , and (meth)acrylic acid was finally obtained from a (meth)acrylic acid recovery stream 320 including the (meth)acrylic acid, and a mother liquor was supplied to the absorption column 100 through a mother liquor circulation line 310 .
  • the amount of the (meth)acrylic acid included in the (meth)acrylic acid recovery stream 320 was 99.5 wt % or more.
  • Example 2 the (meth)acrylic acid was prepared by the same process flow as in Example 1, except that the second (meth)acrylic acid solution discharged from the height of 77% from top to bottom of the absorption column 100 was supplied to the crystallizer.
  • the second (meth)acrylic acid solution included (meth)acrylic acid (88.8 wt %), acetic acid (2.2 wt %), water (5.4 wt %), furfural (3.2 wt %), and maleic acid (0.04 wt %).
  • the amount of the (meth)acrylic acid in the (meth)acrylic acid recovery stream 320 was 99.5 wt % or more, thereby obtaining the (meth)acrylic acid.
  • the amount of the (meth)acrylic acid included in the upper discharge stream 110 of the absorption column was 0.25 mol %.
  • Example 1 when a discharge height of the side discharge stream of the absorption column was controlled to be higher than Example 1, the loss amount of the (meth)acrylic acid discharged as the upper discharge stream of the absorption column was 0.25 mol %, which was confirmed to be increased as compared with the loss amount of the (meth)acrylic acid in Example 1.
  • the (meth)acrylic acid solution was not obtained from the side portion and the bottom of the absorption column 100 , respectively, but obtained only from the bottom of the absorption column, and was added to the crystallizer 300 to obtain (meth)acrylic acid.
  • the mother liquor 310 after crystallization was added to the high-boiling point by-product separation column 200 to obtain a lower discharge stream 220 of the high-boiling point by-product separation column including the high-boiling point by-products and an upper discharge stream 210 of the high-boiling point by-product separation column including the mother liquor from which the high-boiling point by-products were removed.
  • the upper discharge stream 210 of the high-boiling point by-product separation column was recirculated to the absorption column 100 .
  • the (meth)acrylic acid was prepared in the same manner as in Example 1, except the above.
  • the (meth)acrylic acid solution included (meth)acrylic acid (90.5 wt %), acetic acid (1.8 wt %), water (5.9 wt %), furfural (0.7 wt %), and maleic acid (0.7 wt %).
  • the (meth)acrylic acid solution was added to the crystallizer 300 , and it was confirmed that the amount of (meth)acrylic acid in the (meth)acrylic acid recovery stream 320 was 99.5 wt % or more.

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US18/707,678 2022-08-30 2023-08-24 Method for preparation of high-purity (meth)acrylic acid Pending US20250197340A1 (en)

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KR20220109412 2022-08-30
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KR1020230106990A KR20240031050A (ko) 2022-08-30 2023-08-16 고순도 아크릴산의 제조방법
KR10-2023-0106990 2023-08-16
PCT/KR2023/012550 WO2024049101A1 (ko) 2022-08-30 2023-08-24 고순도 (메트)아크릴산의 제조방법

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US7183428B2 (en) * 2003-06-05 2007-02-27 Nippon Shokubai Co., Inc. Method for production of acrylic acid
KR100999428B1 (ko) * 2006-01-20 2010-12-09 니폰 쇼쿠바이 컴파니 리미티드 (메타)아크릴산의 제조 방법
BR112013022304B1 (pt) * 2011-03-11 2020-01-28 Lg Chemical Ltd método de recuperação contínua de ácido (met)acrílico
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